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EP0707794A1 - Disinfectant composition - Google Patents

Disinfectant composition Download PDF

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Publication number
EP0707794A1
EP0707794A1 EP95307484A EP95307484A EP0707794A1 EP 0707794 A1 EP0707794 A1 EP 0707794A1 EP 95307484 A EP95307484 A EP 95307484A EP 95307484 A EP95307484 A EP 95307484A EP 0707794 A1 EP0707794 A1 EP 0707794A1
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EP
European Patent Office
Prior art keywords
chlorhexidine
ethyl alcohol
disinfectant composition
acid
disinfectant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP95307484A
Other languages
German (de)
French (fr)
Other versions
EP0707794B1 (en
Inventor
Yasuo c/o Shiseido Research Center Igarashi (2)
Takashi c/o Shiseido Research Center Suzuki (2)
Tomoko c/o Shiseido Research Center Kimura (2)
Akira c/o Shiseido Research Center Motoyama (2)
Rina c/o Shiseido Research Center Fukuhara (2)
Atsuko c/o Shiseido Research Center Torii (2)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shiseido Co Ltd
Original Assignee
Shiseido Co Ltd
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Filing date
Publication date
Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd
Publication of EP0707794A1 publication Critical patent/EP0707794A1/en
Application granted granted Critical
Publication of EP0707794B1 publication Critical patent/EP0707794B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof

Definitions

  • the present invention relates to a disinfectant composition and, in particular, to stabilization of chlorhexidine in an ethyl alcohol base.
  • Chlorhexidine is a compound which is formally called 1,1-hexamethylenebis [5-(4-chlorophenyl) biguanide]. Due to its continuous and wide disinfecting action, this compound has been compounded as a germicidal prophylactic agent for diseases, an antiseptic, a deodorant, or an anti-inflammatory agent in drugs for pyorrhea, disinfectants, and the like.
  • chlorhexidine which has a sufficient germicidal action, may be added to ethyl alcohol. It has nevertheless been known that, while chlorhexidine is stable in aqueous solution systems since it is inherently water- soluble, its stability is low in ethyl alcohol bases.
  • the ethanol content in such a mixture is at the same level as that in disinfectant ethanol.
  • an object of the present invention is to provide a disinfectant composition in which chlorhexidine is stably compounded in a highly concentrated ethyl alcohol solution.
  • chlorhexidine can stably be compounded in a highly concentrated ethyl alcohol solution when an organic acid is added thereto and thus the present invention has been accomplished.
  • the disinfectant composition in accordance with the present invention is characterized in that it contains ethyl alcohol with a concentration of not lower than 50% by weight, chlorhexidine, and an organic acid.
  • the system of the present invention has a pH from 3 to 5.
  • the organic acid is selected from the group consisting of organic acids having a carbon number from 2 to 16.
  • the organic acid is soluble to an ethyl alcohol solution having a concentration of not lower than 50% by weight and able to adjust the pH of the system from 3 to 5.
  • Examples of such an organic acid include acetic acid, lactic acid, maleic acid, malic acid, citric acid, salicylic acid, myristic acid, and palmitic acid.
  • acetic acid and citric acid are preferable in particular.
  • glycyrrhizinic acid and its derivatives drugs such as vitamin E, vitamin E acetate, and vitamin B6; water- soluble polymers such as xanthan gum, dextrin, hydroxyethyl cellulose, hydroxymethyl cellulose, methyl cellulose, carrageenan, and carboxymethyl cellulose; and the like may be compounded.
  • nonionic surfactants and, in order to increase skin- protecting power, urea or the like may be compounded so as to impart a cleaning effect to the composition.
  • the present invention provides a disinfectant composition used for disinfecting hands and fingers.
  • the present invention provides a method of disinfecting fingers and hands in which the disinfectant composition for disinfecting fingers and hands are used.
  • Fig. 1 is a graph explaining the relationship between the ratio of remaining chlorhexidine in citric acid and lactic acid systems and the pH in these systems.
  • aqueous solutions with the ethyl alcohol concentrations listed below and a chlorhexidine content of 0.2% W/V were prepared and then stored for one month each at 50°C and 0°C. Thereafter, chlorhexidine therein was quantitatively determined. The remaining ratio is calculated as the ratio of the amount of chlorhexidine remaining at 50°C with respect to that at 0°C which is taken as 100%.
  • the concentration thereof should be not lower than 50% by weight or, more preferably, not lower than 70% by weight.
  • the concentration of ethyl alcohol in the mixture was 80% V/V, while each additive was added thereto so as to attain a content of 0.1% W/V.
  • the stability of chlorhexidine in the resulting mixture was evaluated in the same manner as noted above.
  • organic acids having a carbon number from 2 to 16 such as citric acid and lactic acid had a remarkably high stability- imparting action.
  • citric acid, lactic acid, and the like are preferable as compounds which can adjust, with a small amount thereof being added, the pH of the solution having an ethyl alcohol concentration of not lower than 50% by weight from 3 to 5.
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g Cationic surfactant 0.02 Glyceryl triisooctanate 0.4 Citric acid 0.1 Purified water 18.0 Ethanol q.s. to make 100 ml
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g Cationic surfactant 0.02 Glyceryl triisooctanate 0.4 Lactic acid 0.1 Purified water 18.0 Ethanol q.s. to make 100 ml
  • chlorhexidine can be compounded therein very stably even when the ethyl alcohol concentration therein is not lower than 50% by weight, thereby satisfying the germicidal property and quick- dryness of the disinfectant.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

A disinfectant composition contains ethyl alcohol with a concentration of not lower than 50% by weight, chlorhexidine, and an organic acid. Even when the concentration of ethyl alcohol is not lower than 50% by weight, chlorhexidine can be compounded therein very stably.

Description

    [FIELD OF THE INVENTION]
  • The present invention relates to a disinfectant composition and, in particular, to stabilization of chlorhexidine in an ethyl alcohol base.
    • [BACKGROUND OF THE INVENTION]
  • Chlorhexidine is a compound which is formally called 1,1-hexamethylenebis [5-(4-chlorophenyl) biguanide]. Due to its continuous and wide disinfecting action, this compound has been compounded as a germicidal prophylactic agent for diseases, an antiseptic, a deodorant, or an anti-inflammatory agent in drugs for pyorrhea, disinfectants, and the like.
  • Also, as hospital infection within a hospital has often been reported in paper recently, a demand for compounds such as chlorhexidine which can be used in a wide range of disinfection is expected to increase.
  • In the hospital infection within a hospital, it has been reported that there are cases where an infection is transferred from one patient to another patient by way of doctors and nurses. Accordingly, it is necessary for them to disinfect their hands and fingers completely and rapidly after treating or taking care of one patient before treating or taking care of another patient.
  • Therefore, various kinds of quick-drying disinfectants which are mainly composed of ethyl alcohol have recently been studied.
  • However, it is insufficient for quick-drying ethyl alcohol alone to disinfect hands and fingers. Accordingly, chlorhexidine, which has a sufficient germicidal action, may be added to ethyl alcohol. It has nevertheless been known that, while chlorhexidine is stable in aqueous solution systems since it is inherently water- soluble, its stability is low in ethyl alcohol bases.
  • On the other hand, in order to maintain quick- dryness and germicidal power, it is preferable for the ethanol content in such a mixture to be at the same level as that in disinfectant ethanol. Though there is a demand for development of disinfectants in which chlorhexidine is stably compounded while maintaining the germicidal property and quick- dryness, no products have been found sufficiently satisfactory.
    • [SUMMARY OF THE INVENTION]
  • In view of the foregoing problems of the prior art, an object of the present invention is to provide a disinfectant composition in which chlorhexidine is stably compounded in a highly concentrated ethyl alcohol solution.
  • As a result of diligent studies of the inventors to attain the above-mentioned object, it has been found that chlorhexidine can stably be compounded in a highly concentrated ethyl alcohol solution when an organic acid is added thereto and thus the present invention has been accomplished.
  • Namely, the disinfectant composition in accordance with the present invention is characterized in that it contains ethyl alcohol with a concentration of not lower than 50% by weight, chlorhexidine, and an organic acid.
  • Preferably, the system of the present invention has a pH from 3 to 5.
  • Preferably, the organic acid is selected from the group consisting of organic acids having a carbon number from 2 to 16.
  • Preferably, the organic acid is soluble to an ethyl alcohol solution having a concentration of not lower than 50% by weight and able to adjust the pH of the system from 3 to 5.
  • Examples of such an organic acid include acetic acid, lactic acid, maleic acid, malic acid, citric acid, salicylic acid, myristic acid, and palmitic acid. Among them, lactic acid and citric acid are preferable in particular.
  • Also, other ingredients may be compounded in the disinfectant composition in accordance with the present invention. For example, glycyrrhizinic acid and its derivatives; drugs such as vitamin E, vitamin E acetate, and vitamin B6; water- soluble polymers such as xanthan gum, dextrin, hydroxyethyl cellulose, hydroxymethyl cellulose, methyl cellulose, carrageenan, and carboxymethyl cellulose; and the like may be compounded.
  • Further, nonionic surfactants and, in order to increase skin- protecting power, urea or the like may be compounded so as to impart a cleaning effect to the composition.
  • In one aspect, the present invention provides a disinfectant composition used for disinfecting hands and fingers.
  • In another aspect, the present invention provides a method of disinfecting fingers and hands in which the disinfectant composition for disinfecting fingers and hands are used.
    • [BRIEF DESCRIPTIONS OF THE DRAWING]
  • Fig. 1 is a graph explaining the relationship between the ratio of remaining chlorhexidine in citric acid and lactic acid systems and the pH in these systems.
    • [EXAMPLES]
  • In the following, preferable examples of the present invention will be explained. However, the present invention is not restricted to these examples.
    • Stability of Chlorhexidine vs. Ethyl Alcohol Concentration
  • First, the inventors studied the relationship between ethyl alcohol concentration and stability of chlorhexidine.
  • The aqueous solutions with the ethyl alcohol concentrations listed below and a chlorhexidine content of 0.2% W/V were prepared and then stored for one month each at 50°C and 0°C. Thereafter, chlorhexidine therein was quantitatively determined. The remaining ratio is calculated as the ratio of the amount of chlorhexidine remaining at 50°C with respect to that at 0°C which is taken as 100%.
  • The results are shown in TABLE 1. TABLE 1
    Ethyl alcohol conc. 0 10 20 30 40 50 60 70 80
    Remaining ratio 100 95 81 75 69 65 58 53 48
  • On the other hand, when quick- dryness and germicidal power are expected to be improved by ethyl alcohol, the concentration thereof should be not lower than 50% by weight or, more preferably, not lower than 70% by weight.
  • Accordingly, the inventors studied how to improve the stability of chlorhexidine in highly concentrated ethyl alcohol.
    • Stability vs. Various Additives
  • In order to stabilize chlorhexidine in ethyl alcohol, the inventors added various materials, which hardly affected human bodies, to a mixture of chlorhexidine and ethyl alcohol.
  • The concentration of ethyl alcohol in the mixture was 80% V/V, while each additive was added thereto so as to attain a content of 0.1% W/V. The stability of chlorhexidine in the resulting mixture was evaluated in the same manner as noted above.
  • The results are shown in TABLE 2. TABLE 2
    Additive Remaining ratio
    Allantoin
    92%
    Glycine 91%
    Citric acid 99%
    Lactic acid 99%
    Butyl hydroxy toluene 91%
    Tocopherol 94%
  • As shown in TABLE 2, it was found that, among various additives, organic acids having a carbon number from 2 to 16 such as citric acid and lactic acid had a remarkably high stability- imparting action.
    • Stability vs. System pH Changed by Addition of Organic Acid
  • Next, in a system having an ethyl alcohol concentration of 80% by weight, the stability of chlorhexidine was evaluated while the pH of the system was changed by the amount of organic acids being added thereto. The stability was evaluated in the same manner as noted above. Since it was difficult to directly determine the pH in a highly concentrated alcohol system, purified water, which had once been boiled and cooled, was added to 5 g of the sample liquid to yield a solution having a whole amount of 50 g. While thus obtained solution was stirred at room temperature, the pH thereof was determined.
  • The results are shown in Fig. 1.
  • As clearly shown in this drawing, advantageous effects were recognized at the region where pH was from 3 to 5. In particular, the optimum region for stabilizing chlorhexidine existed near a pH of 4.
  • As a result, it is understood that citric acid, lactic acid, and the like, as noted above, are preferable as compounds which can adjust, with a small amount thereof being added, the pH of the solution having an ethyl alcohol concentration of not lower than 50% by weight from 3 to 5.
  • In the following, more specific compounding examples of disinfectant compositions in which chlorhexidine was stably compounded will be described.
    • COMPOUNDING EXAMPLE 1
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g
    Cationic surfactant 0.02
    Glyceryl triisooctanate 0.4
    Citric acid 0.1
    Purified water 18.0
    Ethanol q.s. to make 100 ml
    • COMPOUNDING EXAMPLE 2
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g
    Cationic surfactant 0.02
    Glyceryl triisooctanate 0.4
    Lactic acid 0.1
    Purified water 18.0
    Ethanol q.s. to make 100 ml
  • Both disinfectant compositions in accordance with these compounding examples exhibited an excellent stability.
  • As explained in the foregoing, in the disinfectant composition in accordance with the present invention, as an organic acid is added thereto, chlorhexidine can be compounded therein very stably even when the ethyl alcohol concentration therein is not lower than 50% by weight, thereby satisfying the germicidal property and quick- dryness of the disinfectant.

Claims (6)

  1. A disinfectant composition containing ethyl alcohol with a concentration of not lower than 50% by weight, chlorhexidine, and an organic acid.
  2. The disinfectant composition according to claim 1, wherein a system of said composition has a pH from 3 to 5.
  3. The disinfectant composition according to claim 1 or 2, wherein said organic acid is selected from the group consisting of organic acids having a carbon number from 2 to 16.
  4. The disinfectant composition according to one of claims 1 to 3, wherein said organic acid is at least one of lactic acid and citric acid.
  5. The disinfectant composition according to one of claims 1 to 4, wherein said composition is used for disinfecting hands and fingers.
  6. A method of disinfecting fingers and hands, wherein the disinfectant composition according to claim 5 is used for disinfecting fingers and hands.
EP95307484A 1994-10-21 1995-10-20 Disinfectant composition Expired - Lifetime EP0707794B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP28297694 1994-10-21
JP282976/94 1994-10-21
JP28297694A JP3515821B2 (en) 1994-10-21 1994-10-21 Disinfecting composition

Publications (2)

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EP0707794A1 true EP0707794A1 (en) 1996-04-24
EP0707794B1 EP0707794B1 (en) 2001-04-11

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US (1) US5800827A (en)
EP (1) EP0707794B1 (en)
JP (1) JP3515821B2 (en)
KR (2) KR100414599B1 (en)
AU (1) AU694264B2 (en)
DE (1) DE69520639T2 (en)

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WO1998044800A1 (en) * 1997-04-04 1998-10-15 Henkel-Ecolab Gmbh & Co. Ohg Disinfection method
WO2006062846A3 (en) * 2004-12-09 2007-01-18 Dial Corp Compositions having a high antiviral and antibacterial efficacy
WO2007058995A1 (en) * 2005-11-10 2007-05-24 Ringer Eric M Manually actuated contactless card
WO2007044032A3 (en) * 2004-12-09 2008-03-06 Dial Corp Compositions having a high antiviral and antibacterial efficacy
WO2011063928A3 (en) * 2009-11-24 2011-11-10 Fresenius Medical Care Deutschland Gmbh Disinfectant composition
US8119115B2 (en) 2006-02-09 2012-02-21 Gojo Industries, Inc. Antiviral method
US8450378B2 (en) 2006-02-09 2013-05-28 Gojo Industries, Inc. Antiviral method
US9629361B2 (en) 2006-02-09 2017-04-25 Gojo Industries, Inc. Composition and method for pre-surgical skin disinfection
WO2017137818A1 (en) 2016-02-12 2017-08-17 Salicylates & Chemicals Synthesis and application of an antimicrobial active
WO2020055716A1 (en) * 2018-09-14 2020-03-19 3M Innovative Properties Company Antimicrobial compositions comprising chlorhexidine

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JP3636611B2 (en) * 1999-03-19 2005-04-06 日華化学株式会社 Disinfectant composition
US6899897B2 (en) 2001-06-18 2005-05-31 Jaleva, Inc. Gum resin as a carrier for topical application of pharmacologically active agents
EP1530485A1 (en) 2002-08-20 2005-05-18 Alda Pharmaceuticals Corp. A wide spectrum disinfectant
US9028852B2 (en) * 2004-09-07 2015-05-12 3M Innovative Properties Company Cationic antiseptic compositions and methods of use
US20060074029A1 (en) * 2004-10-04 2006-04-06 Scott Leece Topical antimicrobial composition having improved moisturization properties
US20090012174A1 (en) * 2004-12-09 2009-01-08 The Dial Corporation Compositions Having a High Antiviral and Antibacterial Efficacy
US20080095814A1 (en) * 2004-12-09 2008-04-24 The Dial Corporation Compositions Having a High Antiviral and Antibacterial Efficacy
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RU2008151178A (en) * 2006-05-24 2010-06-27 Дзе Дайл Корпорейшн (Us) METHODS AND PRODUCTS POSSESSING A STRONG ANTI-VIRAL AND ANTIBACTERIAL ACTION
RU2008151763A (en) * 2006-05-26 2010-07-10 Дзе Дайл Корпорейшн (Us) METHOD FOR VIRUS TRANSFER INHIBITION
US8034844B2 (en) * 2006-05-30 2011-10-11 The Dial Corporation Compositions having a high antiviral efficacy
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US9578879B1 (en) 2014-02-07 2017-02-28 Gojo Industries, Inc. Compositions and methods having improved efficacy against spores and other organisms
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CN104622852B (en) * 2015-02-10 2017-08-25 山东天达有限公司 A kind of polysaccharide-modified ethanol water and its preparation method and application
US10813357B1 (en) * 2015-05-26 2020-10-27 Gojo Industries, Inc. Compositions and methods with efficacy against spores and other organisms
DE102015122276A1 (en) 2015-12-18 2017-06-22 Schülke & Mayr GmbH Alcoholic compositions containing octenidine dihydrochloride
DE102015122263A1 (en) 2015-12-18 2017-06-22 Schülke & Mayr GmbH Alcoholic disinfectant for the control of viruses
US10813892B2 (en) 2016-05-24 2020-10-27 Carefusion 2200, Inc. Antiseptic solutions and applicators
WO2020210789A1 (en) 2019-04-12 2020-10-15 Ecolab Usa Inc. Hard surface cleaning solution with rapid viricidal activity
KR102267156B1 (en) 2020-12-23 2021-06-21 주식회사 비바케어 (Composition for sterilization or disinfection and manufacturing method thereof
CN116530515B (en) * 2022-01-26 2025-08-19 上海交通大学 Disinfection product based on citric acid and natural naphthoquinone compounds

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998044800A1 (en) * 1997-04-04 1998-10-15 Henkel-Ecolab Gmbh & Co. Ohg Disinfection method
US6517852B1 (en) 1997-04-04 2003-02-11 Ecolab Gmbh Co. Ohg Disinfection method
WO2006062846A3 (en) * 2004-12-09 2007-01-18 Dial Corp Compositions having a high antiviral and antibacterial efficacy
WO2007044032A3 (en) * 2004-12-09 2008-03-06 Dial Corp Compositions having a high antiviral and antibacterial efficacy
CN101232807A (en) * 2004-12-09 2008-07-30 日晷公司 Compositions with high antiviral and antibacterial efficacy
RU2366460C2 (en) * 2004-12-09 2009-09-10 Дзе Дайл Корпорэйшн Compositions with high antiviral and antibacterial action
CN101232807B (en) * 2004-12-09 2012-12-05 日晷公司 Compositions having a high antiviral and antibacterial efficacy
WO2007058995A1 (en) * 2005-11-10 2007-05-24 Ringer Eric M Manually actuated contactless card
US8119115B2 (en) 2006-02-09 2012-02-21 Gojo Industries, Inc. Antiviral method
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KR100414599B1 (en) 2004-03-06
DE69520639T2 (en) 2001-08-02
AU3439895A (en) 1996-05-02
JPH08119811A (en) 1996-05-14
KR960013197A (en) 1996-05-22
US5800827A (en) 1998-09-01
EP0707794B1 (en) 2001-04-11
DE69520639D1 (en) 2001-05-17
JP3515821B2 (en) 2004-04-05
KR100437566B1 (en) 2004-06-30
AU694264B2 (en) 1998-07-16

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